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Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles

Academic Article
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Overview

related to degree

  • Soenen, Danielle, Ph.D. in Chemistry, Scripps Research 1998 - 2003
  • Wolkenberg, Scott, Ph.D. in Chemistry, Scripps Research 1998 - 2003
  • Wilkie, Gordon, Ph.D. in Chemistry, Scripps Research 1997 - 2002

authors

  • Wilkie, Gordon
  • Elliott, G. I.
  • Blagg, B. S. J.
  • Wolkenberg, Scott
  • Soenen, Danielle
  • Miller, M. M.
  • Pollack, S.
  • Boger, Dale

publication date

  • 2002

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The scope of intramolecular Diels-Alder and a novel tandem Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles is disclosed. In the cases examined, the tandem cycloadditions construct three new rings with formation of four new C-C bonds and set all six stereocenters about a central six-membered ring in a single step including three contiguous and four total quaternary centers without a trace of a second diastereomer.

subject areas

  • Cyclization
  • Oxadiazoles
  • Vinblastine
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja027533n

PubMed ID

  • 12236743
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Additional Document Info

start page

  • 11292

end page

  • 11294

volume

  • 124

issue

  • 38

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